SG177740A1

SG177740A1 - Substituted benzoimidazolesulfonamides and substituted indolesulfonamides as mglur4 potentiators

Substituted benzoimidazolesulfonamides and substituted indolesulfonamides as mglur4 potentiators Download PDF

Info

Publication number: SG177740A1
Authority: SG; Singapore
Prior art keywords: optionally substituted; hydrogen; compound; mglur4; organic residue
Prior art date: 2009-07-23

Application number

SG2012005047A

Other languages

English (en)

Inventor

P Jeffrey Conn

Craig W Lindsley

Corey R Hopkins

Charles David Weaver

Colleen M Niswender

Yiu-Yin Cheung

Original Assignee

Univ Vanderbilt

Priority date

2009-07-23

Filing date

2010-07-23

Publication date

2012-02-28

2010-07-23 Application filed by Univ Vanderbilt filed Critical Univ Vanderbilt

2012-02-28 Publication of SG177740A1 publication Critical patent/SG177740A1/en

Links

XRGHQBXKSHAQRB-UHFFFAOYSA-N 1h-benzimidazole-2-sulfonamide Chemical class C1=CC=C2NC(S(=O)(=O)N)=NC2=C1 XRGHQBXKSHAQRB-UHFFFAOYSA-N 0.000 title abstract description 3
RYMYQAMZUWJAEO-UHFFFAOYSA-N 1h-indole-2-sulfonamide Chemical class C1=CC=C2NC(S(=O)(=O)N)=CC2=C1 RYMYQAMZUWJAEO-UHFFFAOYSA-N 0.000 title abstract description 3
102100038354 Metabotropic glutamate receptor 4 Human genes 0.000 claims abstract description 54
108010038422 metabotropic glutamate receptor 4 Proteins 0.000 claims abstract 50
150000001875 compounds Chemical class 0.000 claims description 362
-1 s- butyl Chemical group 0.000 claims description 349
229910052739 hydrogen Inorganic materials 0.000 claims description 255
239000001257 hydrogen Substances 0.000 claims description 253
238000000034 method Methods 0.000 claims description 235
150000002431 hydrogen Chemical class 0.000 claims description 161
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 135
229910052757 nitrogen Inorganic materials 0.000 claims description 134
125000003545 alkoxy group Chemical group 0.000 claims description 123
150000004820 halides Chemical class 0.000 claims description 116
230000000694 effects Effects 0.000 claims description 115
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 108
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 107
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 106
125000004093 cyano group Chemical group *C#N 0.000 claims description 106
125000005518 carboxamido group Chemical group 0.000 claims description 105
DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims description 105
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 105
125000000753 cycloalkyl group Chemical group 0.000 claims description 97
241000124008 Mammalia Species 0.000 claims description 90
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 88
208000035475 disorder Diseases 0.000 claims description 84
239000000203 mixture Substances 0.000 claims description 73
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 69
239000003814 drug Substances 0.000 claims description 64
125000004122 cyclic group Chemical group 0.000 claims description 62
230000004064 dysfunction Effects 0.000 claims description 62
238000011282 treatment Methods 0.000 claims description 60
229940079593 drug Drugs 0.000 claims description 54
102000005962 receptors Human genes 0.000 claims description 52
108020003175 receptors Proteins 0.000 claims description 52
201000010099 disease Diseases 0.000 claims description 51
150000003839 salts Chemical class 0.000 claims description 49
108010010914 Metabotropic glutamate receptors Proteins 0.000 claims description 43
102000016193 Metabotropic glutamate receptors Human genes 0.000 claims description 43
239000000556 agonist Substances 0.000 claims description 43
125000003118 aryl group Chemical group 0.000 claims description 39
239000008194 pharmaceutical composition Substances 0.000 claims description 39
230000003389 potentiating effect Effects 0.000 claims description 39
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 37
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 37
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 37
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 36
125000001072 heteroaryl group Chemical group 0.000 claims description 36
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
210000004027 cell Anatomy 0.000 claims description 33
125000000392 cycloalkenyl group Chemical group 0.000 claims description 32
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 28
229930195712 glutamate Natural products 0.000 claims description 28
239000003795 chemical substances by application Substances 0.000 claims description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 24
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 24
230000005062 synaptic transmission Effects 0.000 claims description 24
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125000003373 pyrazinyl group Chemical group 0.000 claims description 23
125000002098 pyridazinyl group Chemical group 0.000 claims description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
239000003937 drug carrier Substances 0.000 claims description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 21
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125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 19
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125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 18
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 18
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 18
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 18
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125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
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125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 18
230000001965 increasing effect Effects 0.000 claims description 17
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 16
208000012902 Nervous system disease Diseases 0.000 claims description 15
230000000926 neurological effect Effects 0.000 claims description 15
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125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 13
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical compound C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 claims description 10
CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 claims description 10
UPNNXUSUOSTIIM-UHFFFAOYSA-N 1,2-dithietane Chemical compound C1CSS1 UPNNXUSUOSTIIM-UHFFFAOYSA-N 0.000 claims description 10
DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims description 10
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 10
IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 claims description 10
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 10
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 10
JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 10
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 10
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230000036506 anxiety Effects 0.000 claims description 10
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DIXBSCZRIZDQGC-UHFFFAOYSA-N diaziridine Chemical compound C1NN1 DIXBSCZRIZDQGC-UHFFFAOYSA-N 0.000 claims description 10
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HGGNZMUHOHGHBJ-UHFFFAOYSA-N dioxepane Chemical compound C1CCOOCC1 HGGNZMUHOHGHBJ-UHFFFAOYSA-N 0.000 claims description 10
ASQQEOXYFGEFKQ-UHFFFAOYSA-N dioxirane Chemical compound C1OO1 ASQQEOXYFGEFKQ-UHFFFAOYSA-N 0.000 claims description 10
WXIXHCWLYVANJA-UHFFFAOYSA-N dioxocane Chemical compound C1CCCOOCC1 WXIXHCWLYVANJA-UHFFFAOYSA-N 0.000 claims description 10
LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims description 10
KUSGATRNQCYALG-UHFFFAOYSA-N dithiepane Chemical compound C1CCSSCC1 KUSGATRNQCYALG-UHFFFAOYSA-N 0.000 claims description 10
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LMBQHCNXCQCXGQ-UHFFFAOYSA-N dithiocane Chemical compound C1CCCSSCC1 LMBQHCNXCQCXGQ-UHFFFAOYSA-N 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 10
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
IVMHDOBGNQOUHO-UHFFFAOYSA-N oxathiane Chemical compound C1CCSOC1 IVMHDOBGNQOUHO-UHFFFAOYSA-N 0.000 claims description 10
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